A rapidly growing vacation rental property management company is seeking an experienced Regional President to lead a significant multi-market portfolio across several high-profile leisure and resort destinations.

This is a highly visible senior leadership opportunity for a strategic and hands-on operator who combines strong financial discipline, operational excellence, people leadership, and growth orientation. The Regional President will have broad accountability for regional performance, including the consolidated P&L, revenue and EBITDA performance, market growth, operational execution, and the development of high-performing General Manager teams.

The successful candidate will serve as the critical connection between corporate leadership and local market operations, ensuring that company strategy translates into consistent execution while maintaining the entrepreneurial mindset and local accountability necessary to succeed in a multi-market vacation rental environment.

Note: This is a remote plus up to 50% travel position, requiring the individual to reside anywhere within Eastern or Central time zones

Key Responsibilities

• Own regional financial performance: Oversee the consolidated P&L, revenue, EBITDA, forecasting, budgeting, and financial accountability across 6–10 markets.
• Drive operational excellence: Ensure consistent operating standards across housekeeping, maintenance, guest services, and onboarding while improving efficiency and service quality.
• Lead and develop General Managers: Coach, develop, and hold GMs accountable for market performance, while building a strong pipeline of high-performing leaders.
• Drive growth: Increase unit count, revenue, and market share through owner acquisition, retention, local partnerships, marketing, and business development initiatives.
• Lead acquisition integration: Oversee the integration of acquired businesses, ensuring alignment with company systems, financial reporting, technology, and operating standards.
• Partner with executive leadership: Serve as the connection between corporate leadership and local operations, helping implement company-wide initiatives and providing field-level insight.
• Maintain strong market visibility: Spend significant time in the assigned markets, with approximately 50% travel, to build relationships, assess performance, and ensure execution.

Ideal Candidate Profile

The ideal candidate will be an accomplished multi-unit, multi-market hospitality or vacation rental executive who has demonstrated success managing significant revenue responsibility and leading through General Managers or other senior market leaders.

• Proven P&L ownership and strong financial acumen, including experience managing revenue, EBITDA, labor costs, forecasting, and operating performance.
• Experience overseeing multiple markets, locations, or business units simultaneously.
• Demonstrated responsibility for a business or portfolio generating at least $25 million in annual revenue.
• A track record of driving profitable growth, market share, and unit or customer growth.
• Strong operational leadership and a demonstrated ability to improve consistency and execution across geographically dispersed teams.
• Experience recruiting, developing, and holding General Managers and senior leaders accountable for results.
• An entrepreneurial mindset balanced with the ability to implement scalable processes and operating standards.
• Experience integrating acquisitions or leading organizations through significant growth and change is highly valued.
• Strong analytical and data-driven decision-making skills.
• Excellent communication and relationship-building abilities with both corporate executives and local market teams.
• The willingness and ability to maintain a highly visible presence across the region, including approximately 50% travel.

Compensation: $200,000 - $245,000 base salary (commensurate with experience), 25-35% bonus program, comprehensive health, dental, and vision, 401k with company match, unlimited PTO, and much more!

This is an opportunity to join a growing company at an important stage of its evolution. The Regional President will have substantial influence over the performance and future growth of a significant portion of the organization and will play a key role in creating the structure, accountability, and leadership necessary to scale successfully.

The position is particularly well suited for a senior hospitality or vacation rental executive who enjoys owning results, developing leaders, improving operations, and building businesses across multiple markets.

This search is being conducted on a confidential basis. Additional information regarding the company, portfolio, compensation, and specific markets will be shared with qualified candidates during the interview process.

Please apply with an updated resume if you are interested in being considered.

only qualified candidates will be contacted